Enantioselective N-Heterocyclic Carbene-Catalyzed Cascade Reaction for the Synthesis of Pyrroloquinolines via N-H Functionalization of Indoles

被引：58

作者：

Mukherjee, Subrata ^{[1
,2
]}

Shee, Sayan ^{[3
]}

Poisson, Thomas ^{[4
,5
]}

Besset, Tatiana ^{[4
]}

Biju, Akkattu T. ^{[3
]}

机构：

[1] Natl Chem Lab, CSIR, Organ Chem Div, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India

[3] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

[4] Normandie Univ, INSA Rouen, UNIROUEN, CNRS,COBRA,UMR 6014, F-76000 Rouen, France

[5] Inst Univ France, 1 Rue Descartes, F-75231 Paris, France

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 22期

关键词：

ASYMMETRIC-SYNTHESIS; MODIFIED ENALS; ANNULATION; ALKYLATION; ALDEHYDES; ACYL; ORGANOCATALYSIS; DERIVATIVES; MECHANISM;

D O I：

10.1021/acs.orglett.8b02820

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Functionalization of the indole N-H bond for enantioselective synthesis of biologically important pyrroloquinoline derivatives has been reported under oxidative N-heterocyclic carbene catalysis conditions. The interception of catalytically generated chiral alpha,beta-unsaturated acylazoliums with the indole derivatives proceeds in an aza-Michael/Michael/lactonization sequence to deliver the pyrroloquinoline derivatives in good yields, diastereoselectivities, and enantioselectivities. The simultaneous enhancement of reactivity and selectivity observed in polar aprotic solvents is noteworthy.

引用

页码：6998 / 7002

页数：5

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